What makes a great country song? It tells a story. It draws a line. It has a twang you can feel down to the soles of your feet. Some get mad, some get weepy, some just get you down the road. But these are 100 essential songs that map out the story of country music, from Hank Williams howling at the moon to George Jones pouring one out for all the desperate lovers to Taylor Swift singing the suburban cowgirl blues.

100. Brad Paisley, ‘Welcome to the Future’ (2009)

Mainstream country's most prominent liberal ambitiously overloads this nearly six-minute single from 2009's American Saturday Night, explaining that he wanted "to serve up a little multigenerational truth with a strong sense of hope and possibility." In this bright "Future," Paisley marvels at car DVD players and mobile-phone videogames, imagines how trans-Pacific commerce might amaze his WWII-vet grandfather and then brings his mid-tempo country-rocker down a notch to appreciate the racial progress that has occurred in his own lifetime – he debuted the song live at the White House. Basically, it's a typical Brad Paisley A.D.D. special, mixing synth lines with steel guitar, fiddle breaks with speed riffs and sense with sentiment. By Richard Gehr

99. Harry Choates, ‘Jole Blon’ (1946)

One of Bruce Springsteen's lesser-known influences is the late, hard-drinkin' Texas fiddle player Harry Choates. After playing for spare change as a teenager in the Thirties, Choates started making records by his early Twenties, and his aching 1946 reworking of the so-called "Cajun National Anthem" hit Number Four on the Billboard charts. "Jole Blon," a traditional cajun waltz with nearly indiscernible lyrics about a pretty blonde, rode commercial success via several reinterpretations and continued in country lore throughout the decade. It passed through the hands of Roy Acuff, Warren Zevon, Springsteen (who recorded an early-Eighties version with Gary U.S. Bonds) among many others. Fame and fortune never made it back to Choates, however. According to legend, he sold "Jole Blon" for $100 and a bottle of whiskey and died at the age of 28. By Reed Fischer

98. C.W. McCall, ‘Convoy’ (1975)

This loving, jargon-filled novelty song took the insular world of trucker culture to the tops of both the country and pop charts in 1976. "Convoy," an ode to C.B. radio, gave Iowa singer C.W. McCall the only Number One hit of his career, sold two million copies, started a C.B. radio fad and even spawned a successful action movie of the same name. "The truckers were forming things called convoys and they were talking to each other on C.B. radios," explained McCall, who co-wrote the song with Chip Davis. "They had a wonderful jargon. Chip and I bought ourselves a C.B. radio and went out to hear them talk." That's a 10-4, good buddy. By Jonathan Bernstein

97. Gretchen Wilson, ‘Redneck Woman’ (2004)

Originally a collective of Nashville outcasts and outsiders known for their open-minded open mic night, the MuzikMafia went mainstream with the twin successes of Big & Rich's "Save a Horse (Ride a Cowboy)" and Gretchen Wilson's "Redneck Woman." With its upbeat swing and beer-drinking, Walmart-wearing identity politics, "Redneck Woman" quickly rose up the charts. Following a breakthrough performance at the 2004 Country Radio Seminar, "Redneck Woman" became the fastest rising Number One since Billy Ray Cyrus' "Achy Breaky Heart." Though Wilson herself was never able to repeat its success, the song paved the way for rocking female bad-asses like Miranda Lambert and Kimberly Perry. By Nick Murray

96. Ronnie Milsap, ‘Smoky Mountain Rain’ (1980)

This story of returning home from the city was told through thunderous piano playing (inspired by Milsap's session work on Elvis' "Kentucky Rain") and producer Tom Collins' spiralling strings. Of course, "Smoky Mountain Rain" wouldn't be on this list if the words weren't equally chilling: Note, for instance, that before the protagonist heads back to North Carolina, he has not change of plans but a "change of dreams." Written by Kye Fleming and Dennis Morgan, who were instructed by Collins to come up with a song about his actual home state, "Smoky Mountain Rain" was Milsap's fourth Number One of 1980 alone. By Nick Murray

95. Bellamy Brothers, ‘Old Hippie’ (1985)

These irresistibly slick opportunists always had a keen eye for cultural shifts: "If I Said You Had a Beautiful Body Would You Hold It Against Me" treated country's late-Seventies transition from the honky-tonk to the singles' bar as a forgone conclusion and 1987's "Country Rap" is pretty self-explanatory. "Old Hippie" is the Brothers' astute take on how onetime counterculture rebels, alienated by disco and new wave, turned to country music in the Eighties with an age-worn weariness: "He ain't tryin' to change nobody/He's just tryin' real hard to adjust." Ten years later, "Old Hippie (The Sequel)" brought us into the Clinton era, and in 2007, on "Old Hippie III (Saved)," our hero was born again. Meanwhile, contemporary country is providing a similar escape for many aging Nineties rock fans. Who's going to write "Old Slacker"? By Keith Harris

94. Dwight Yoakam, ‘Guitars, Cadillacs’ (1986)

Yoakam is often painted as a critic of Nashville, but in "Guitars, Cadillacs" the hillbilly music that Tennessee once produced becomes the only thing that makes Tinsel Town tolerable for this "naive fool who came to Babylon and found out that the pie don't taste so sweet." Of course, despite his posturing, L.A. was the perfect place for the Ohio transplant. A home for country rock since the Byrds and the Burrito Brothers, the ambitious singer found his match in local roots-oriented post-punk acts like the Blasters, Lone Justice and the Knitters. The biggest influence on "Guitars, Cadillacs," however, the one who lent the song its crisp guitar and walking bassline, remained two hours north. His name was Buck Owens, and two years later Yoakam would give him his 21st chart-topper with "Streets of Bakersfield." By Nick Murray

93. Tom T. Hall, ‘Old Dogs, Children and Watermelon Wine’ (1972)

In 1972, country music's consummate storyteller traveled to Miami Beach to perform at the Democratic National Convention that nominated George McGovern and returned to Nashville afterward with a soon-to-be-hit. A janitor, a month away from his 66th birthday, shared his impressions of the only three things worth a damn in life, while casting aspersions on the loyalty and value of lovers and friends – and Hall took it all down. The resulting hit, though sentimental on the surface, has a cynical flipside, its distrust of all but the simplest things in life imparting an aftertaste of sour Seventies disillusion. Nixon won, by the way. By Keith Harris

92. Juice Newton, ‘Queen of Hearts’ (1981)

Originally a member of the short-lived band Silver Spur, Juice Newton had been releasing a steady output of solo pop and rock material for two years – to decent reviews but few sales. When she shifted to a more country sound for 1981's Juice, she scored three Top 10 hits. The breakout track was "Queen of Hearts," the irresistibly catchy, Fleetwood-esque country-pop cut written by Hank DeVito. Newton had been playing the song at her live shows for a year before Richard Landis produced it for the LP. It was all up from there: The LP went platinum in the U.S. and triple platinum in Canada and earned her two Grammy nominations that year. By Cady Drell

91. Garth Brooks, ‘Friends in Low Places’ (1990)

With a voice stirring together the low end of Johnny and the high whine of Hank, Garth Brooks was just beginning his historic superstar run. A couple dozen folks – including "Low Places" songwriters Dewayne Blackwell and Earl "Bud" Lee – partied in the studio to create the bar-storming romp heard on the final refrain. But the party was just starting. The hit helped Brooks' second album, No Fences, ship 17 million copies in the U.S. – still one of the 10 best-selling albums of all time. When Brooks performed "Friends in Low Places" on the Grammys in the early Nineties, the stage was set up like a posh black-tie affair. Just as the song says, the Oklahoma native showed up in boots – as well as a vertical striped shirt, black cowboy hat, and a thumb jabbed into the pocket of his jeans. Eventually the onstage glitz got pushed away to reveal a down-and-dirty saloon, like the ones blasting his song nationwide. By Reed Fischer

90. Ray Wylie Hubbard, ‘Redneck Mother’ (1975)

This second-tier Texas outlaw still writes, performs and records, but he dreamed up his only classic tune (recorded most famously by Jerry Jeff Walker, though Nineties alt-rockers Cracker do a killer version), early in his career, while kicking around in New Mexico. "Redneck Mother" flips a popular slogan among revolutionaries (as in, "Up against the wall…") and flips the bird to country's mother-worship. Never mind what Merle said – mama didn't try hard enough, Hubbard suggests. If she had, maybe there wouldn't be so many good-for-nothing drunks out there "kickin' hippies' asses and raisin' hell." By Keith Harris

89. Gary Stewart, ‘She’s Actin’ Single, I’m Drinkin’ Doubles’ (1975)

A hurtin', cheatin', drinkin' trifecta, Gary Stewart's only Number One would pass for a honky-tonk parody if the Kentucky singer's trembling tenor weren't so convincing. A hardcore-country home run at a time when the genre was heading uptown, "She's Actin' Single" finds Stewart living a perpetual nightmare in which "she pours herself on some stranger" while "I pour myself a drink somewhere." The Wayne Carson–penned tune was the third hit from Stewart's excellent Out of Hand, and the record features both John Hughey playing tear-jerking pedal steel and a mournful chorus from Elvis-affiliated gospel quartet the Jordanaires. An unreconstructed Southern rocker when he wanted to be, Stewart's version of a self-pitying coward struck a chord with a jukebox crowd who sometimes, as Stewart sang elsewhere, "got this drinkin' thing, to keep from thinkin' things." By Richard Gehr

88. Jerry Jeff Walker, ‘Desperados Waiting for a Train’ (1973)

Even back in 1970, Austin was getting weird, and Jerry Jeff Walker, a New York transplant backed by a band called the Lost Gonzos, was leading the transition. On his 1973 live-in-Luckenbach ¡Viva Terlingua! LP, he became the first to record "Desperados Waiting for a Train," a track that another Austin transplant, Guy Clark, wrote while working at a dobro factory in California. Moonlighting as a songwriter, he came up with the title phrase and built around it the story of a grandfather figure to whom he had once been close. "He ended up in west Texas working for Gulf Oil," recalled Clark. "To me, as a kid, he was a real desperado, the real deal. You can't make this shit up." By Marissa R. Moss

87. Lyle Lovett, ‘If I Had a Boat’ (1988)

In the mid-Eighties Lyle Lovett emerged on the bookish, folkie fringe of a new traditionalism that reacted against the pop leaning of the Urban Cowboy era. Consisting of little more than guitars – a finger-picked acoustic and a welling slide – "If I Had a Boat" is nothing to ride a mechanical bull too. And the abstract lyrics, which imagined Roy Rogers as confirmed bachelor and Tonto losing patience with the Lone Ranger, demanded concentration. Absurdist and meditative as it is, "If I Had a Boat" arose from a true story. Lovett claims he once tried to ride a pony across a pond. He wished he'd had a boat. By Keith Harris

86. Donna Fargo, ‘The Happiest Girl in the Whole U.S.A.’ (1972)

Triumphant, hopeful and as corny as Kansas in August, North Carolina native Donna Fargo took this self-composed paean to young newlywed bliss to the top of the country charts. There's no tortured dark-end-of-the-street sentiments for Fargo, who seems to mean every last "skippidy do da." All that honky-tonk ne'er-do-well stuff about drinkin' and cheatin' and carryin' on? That's for middle age. For the two-and-a-half minutes that this lovers' anthem lasts, it can wait. By David Menconi

85. O.B. McClinton, ‘Don’t Let the Green Grass Fool You’ (1972)

After failed attempts at R&B, country pastures were far greener for Osbie Burnett McClinton. Once the Mississippi native became the "Chocolate Cowboy" in the early Seventies, he rolled out a string of charting country hits featuring his rich baritone voice, able backup singers and a wry sense of humor. ("The Other One" corrected anyone mistaking him for Charley Pride.) McClinton's biggest song, off 1972's Obie From Senatobie (via Stax subsidiary Enterprise) was a twangier remake of R&B hit "Don't Let the Green Grass Fool You," which notched Number 37 on the country charts. Originally an early Wilson Pickett single, the perspective of an about-to-be-jilted lover trying to spark that old flame resonates in any genre. By Reed Fischer

84. Neko Case, ‘People Got a Lotta Nerve’ (2009)

Who cares that the song's two protagonists – a killer whale and an elephant – were two unusual subjects for a country song? "I realized that it's OK to admit that no matter who your characters are, you're writing about yourself," Neko Case told the New York Times. The first single from 2009's Middle Cyclone, "People Got a Lotta Nerve" sent a stern warning to anyone foolish enough to tie the singer down. "I'm a man-, man-, maneater," went the chorus, delivered with such poppy playfulness that it was easy to gloss over the song's sinister undertow. By Andrew Leahey

83. Bobby Bare, ‘Streets of Baltimore’ (1966)

This tragic tale of a man who gave up his entire life to make his woman happy in Baltimore (and who gets subsequently dumped there) was originally recorded by Bobby Bare, a singer most famous for working with a young Kris Kristofferson. But, as Bare told Rolling Stone in 1980, "Most of my hits would have been hits for anybody, I just got to 'em first." So it was with "Streets of Baltimore," penned by Tompall & the Glaser Brothers, who wanted to release the single themselves in September of 1966. Unfortunately for them, Bare got to it first (in June) and scored a hit, reaching the Number Seven spot on the country charts. The joke ended up being on Bare, though: For many, Gram Parsons' 1973 version is widely considered the song's most essential incarnation. By Cady Drell

82. Reba McEntire, ‘Fancy’ (1991)

Written and recorded for Bobbie Gentry's 1969 album of the same name, "Fancy" tells a rags-to-riches tale of a young girl whose mother sends her into prostitution. McEntire had wanted to record the song for years, but producer Jimmy Bowen argued against it – not because of the subject matter, but because he felt too many people associated the song with its original performer. When McEntire turned to Tony Brown for her 1990 album, Rumor Has It, the pair gave the song a striking loud-quiet-loud arrangement that helped introduce it to a new generation. By Linda Ryan

81. Gary Allan, ‘Songs About Rain’ (2003)

The second single from Allan's See If I Care tells of a downtrodden masochist who's wasting a perfectly good night driving in circles, listening to a perverse radio station that for some reason keeps playing songs – "Rainy Night In Georgia," "Kentucky Rain," "Here Comes That Rainy Day Feeling Again," "Blue Eyes Crying in the Rain" – that all tell of stormy weather. But where the heartbroken man wallows in these tracks, Allan is busy placing his own in their lineage, successfully conjuring a country classic that's as heartbreaking as the sum of its references. Co-writer Liz Rose, who has since helped pen a handful of hits by Taylor Swift, would later recall how "Songs About Rain" changed her career: "It wasn't until I had the Gary Allan single that I could really say I was a songwriter." By Linda Ryan

80. John Anderson, ‘Wild and Blue’ (1982)

Inspired by a girl who "could party and rock harder than anyone I'd known," John Scott Sherrill wrote this song while separating from his wife. The first country chart-topper for both singer John Anderson and Sherrill, "Wild and Blue" is a hauntingly beautiful account of a cheating woman, told from the POV of her cuckolded man. Anderson's syrupy drawl and mournful wail is intensified by sister Donna's Hill Country harmonizing. Lloyd Green's pedal steel and twin fiddles paint a long, bleak evening of waiting for honey to come home, but in the end the singer's resigned forgiveness is hardly cause for celebration. Big-voiced Sally Timms gave Anderson's 1982 hit a straight, strong reading when British country-punks the Mekons covered it on 1991's Curse of the Mekons. By Richard Gehr

79. Garth Brooks, ‘The Dance’ (1989)

The second Number One single off Garth Brooks' debut LP, "The Dance" is a better-to-have-loved-and-lost slow jam that co-writer Tony Arata had been playing to open mic nights since he had moved to Nashville a few years earlier. "The only folks listening, however, were other songwriters," remembers Arata. When Brooks first heard him play "The Dance," he swore he would record the song if he ever got signed. By Linda Ryan

78. Roger Miller, ‘King of the Road’ (1964)

Inspired by a sign in Chicago that read "Trailers for Sale or Rent," Roger Miller's finger-snapping, bass-walking 1965 hit sold 2.5 million copies and became the Texas-born songwriter's signature tune. Miller's deliciously detailed masterpiece describes a happy-go-lucky vagrant's existential tradeoff: "Two hours of pushin' a broom / Buys an eight-by-12 four-bit room." A perfectly modulated chorus sketches the hobo's sunny familiarity with train engineers' families before sneakily adding his similar acquaintance with "every door that ain't locked when no one's around." Later in '65, singer Jody Miller (no relation) answered with "Queen of the House," a similarly ironic ode to domestic royalty. Roger released his own sequel of sorts in 1970 when he opened Nashville's King of the Road Motor Inn. By Richard Gehr

77. Martina McBride, ‘Independence Day’ (1994)

Songwriter Gretchen Peters wrote "Independence Day" from the point of view of an eight-year-old girl who watched her mother get abused by her alcoholic father, until her mother burns down their house. Its popularity – intrinsically tied to its subject matter – helped McBride become a spokesperson for domestic abuse awareness and raise hundreds of thousands of dollars for charity. But conservative host Sean Hannity wasn't in on the track's deeper meaning, using it as the theme song for his 2001 political radio show. "I know he [was] completely disregarding what the song's about," said Peters, "but… as long as they pay me, that gives me the wherewithal to support causes I believe in, and it all works out." By Cady Drell

76. Jamey Johnson, ‘In Color’ (2008)

Addiction, divorce, despair: Jamey Johnson spilled his demons on 2008's, That Lonesome Song, an album that positioned the Alabamian as an able heir to the outlaw country throne. "I was trying to reach that dude at the bar going through what I was going through," he told Rolling Stone. But where he truly shines is on "In Color," a bittersweet ballad about man trying to convince his grandson that his photos – and his life – were more vibrant than just black and white, displaying a delicate sense for narrative and an emotive voice that's both calloused and vulnerable. Written with James Otto and Lee Thomas Miller, the song was originally cut by Trace Adkins, for whom Johnson had earlier penned the American-as-apple-bottom anthem "Honky Tonk Badonkadonk." "Trace was gracious," Miller later explained. "He told me, 'The guy wrote the song. What am I gonna do?'" By Marissa R. Moss

75. Charlie Rich, ‘Behind Closed Doors’ (1973)

Charlie Rich had been struggling to find a niche between his rocking, jazz-picker roots and the Music Row mainstream for two decades. Then "Behind Closed Doors" gave the so-called Silver Fox the biggest hit of his career. "The jocks had been complaining that [Rich] was too bluesy for country," producer Billy Sherill explained to Billboard in September of 1974. "Others said he was too country for anything else. We just needed the right song." To create that right song, Sherill and Co. started with a riff that writer Kevin O'Dell had been humming for years, and then balanced traditional country flourishes with the dramatic orchestral instrumentation of an 11-piece string section. Rich won two Grammys and his only CMA Entertainer of the Year award. By Marissa R. Moss

74. Lucinda Williams, ‘Passionate Kisses’ (1988)

After recording a pair of acoustic blues albums for Folkways, Lucinda Williams found her rightful audience with her eponymous 1988 Rough Trade debut. It contained this hoarse-voiced pop-rock anthem about not only wanting but deserving a comfortable bed, bath, and emotional beyond. Williams was broke and turning 40 when Mary Chapin Carpenter softened the song's edges, added a stirring guitar arrangement and took "Passionate Kisses" close to the top of the Billboard country chart in 1993, winning Grammys for both herself and its author. By Richard Gehr

73. Dolly Parton, ‘Coat of Many Colors’ (1971)

Parton's most homespun hit (and her frequently avowed favorite) effortlessly transplants the biblical story of Joseph to the postwar Tennessee of Dolly's girlhood, celebrating the unselfconscious pride in a patchwork garment her mama fashioned out of rags. Parton wrote the song on Porter Wagoner's tour bus – and on Porter Wagoner's dry cleaning receipt, the only paper handy when inspiration struck. Wagoner later framed that receipt. The coat itself (or, as Coat Truthers insist, a latter-day recreation) hangs in the Chasing Rainbows Museum at Parton's theme park, Dollywood. By Keith Harris

72. D.L. Menard, ‘The Back Door (La Porte en Arrière)’ (1962)

Born into a Cajun farming family in Erath, Louisiana, in 1932, Doris Leon Menard based this regional hit on "Honky Tonk Blues" by Hank Williams, to whom he always bore a musical resemblance. Written during his shift at a service station, and recorded with Elias Badeaux and the Louisiana Aces, Menard's catchy two-step satirizes a Cajun stereotype, the hard-drinking spendthrift whose late-night escapades lead to an early-morning return through the back door (and ultimately prison). "La Porte d'en Arrière" sold out its initial 300-copy run within days, then sold half a million more while becoming Cajun music's most frequently covered song not titled "Jole Blon." Although Menard soon "came to where I couldn't bear to even hear the name of that song, I got so tired of it," he still manages to perform "La Porte" to this day. By Richard Gehr

71. Alabama, ‘Mountain Music’ (1982)

Years before his band become the most successful country group of the 1980s, Randy Owen spent his childhood days on Lookout Mountain, where his family ran a small cotton farm. 1982's "Mountain Music" paid tribute to those southern roots, setting Owen's adolescent hobbies – river-swimming, tree-climbing, raft-building – to a soundtrack of classic-rock guitar riffs, country harmonies and fiddle-fueled breakdowns. "We did 'Mountain Music' in two cuts," he told CMT. "Back when we had a chance to rehearse and arrange stuff, we just went in and did the song like we'd rehearsed it." Released during a time when country stars rarely played on their own records, "Mountain Music" was the work of a true band, and was proof that no one has to rely on the Nashville hit machine. By Andrew Leahey

70. Lee Ann Womack, ‘I Hope You Dance’ (2000)

In the two decades Lee Ann Womack has been making music, she's never made a splash like the one she made with this 2000 song. It charted at Number One on both the country and adult contemporary charts, won "Song of the Year" at the CMAs, ACMs, ASCAP awards and took home a Grammy for "Best Country Song." Plus, between the years of 2000 and 2007, you couldn't throw a rock at a high school graduation without hitting it. But according to the song's co-writer Tia Sillers, it was actually less about how the children are our future and more about her rough divorce. Still inspirational, just more depressing. By Cady Drell

69. Tammy Wynette, ‘D-I-V-O-R-C-E’ (1968)

Country music's most parodied anthem (see Homer and Jethro paean to a doomed sow, "B-A-C-O-N & E-G-G-S") began, unpromisingly, as "I-L-O-V-E-Y-O-U, Do I have to Spell It Out for You?" Songwriter Bobby Braddock found a juicier subject and song-plugger Carly Putman suggested a sadder melody. Producer Billy Sherrill brought the finished product to Tammy Wynette, whose achingly sincere limning of a mother spelling out the "hurtin' words" in front of her four-year-old made the song her third Number One and the title track of her first gold album. "I hated myself for not writing that song," the five-time divorcée later said. "It fit my life completely." By Richard Gehr

68. John Prine, ‘Angel from Montgomery’ (1971)

When John Prine wrote "Angel" he'd been working as a mailman in the suburbs of Chicago, sketching out ideas as he made the rounds, playing open mics on weekends. At the time, country was cross-pollinating with the distinctly un-country sounds of pop and soft-rock, but Prine presented himself as something more stripped down: A regular guy with a plain voice playing simple music, no shoulder pads necessary. But it was his ear for detail – the flies buzzing around the sink, the rodeo poster that sends a woman on a daydream that she knows will never get fulfilled – that made his songs quietly complicated. Country music rendered with the sharpened eye of an author. By Mike Powell

67. Loretta Lynn, ‘The Pill’ (1975)

Recorded in 1972 but released in 1975, Lynn's ode to reproductive rights turned out to be a difficult pill for many country stations to swallow – one of nine Lynn songs banned during her career. Written by Lorene Allen, Don McHan and T. D. Bayless, "The Pill" uses a chicken-coop metaphor ("I'm tearin' down your brooder house") to warn a straying cock that his hen may start exchanging her maternity-wear "garbage" for clothes that "won't take up so much yardage." Lynn, who birthed four babies by age 20, employs her throaty chuckle-growls to even the scales over funky chicken-scratch guitars. "They didn't have none of them pills when I was younger," Lynn wrote in Coal Miner's Daughter, "or I would have been swallowing 'em like popcorn." By Richard Gehr

66. Rosanne Cash, ‘Seven Year Ache’ (1981)

When Cash recorded "Seven Year Ache" at age 25, it was with the soulful, seen-it-all purr of someone who'd endured the game for decades. And she had: Growing up with dad Johnny's drug addiction, touring absences, divorce from her mom Vivian and second marriage to June Carter which forced her dual Tennessee/California identity; not to mention cultivating her own career, sustaining her first marriage to hotshot singer-songwriter Rodney Crowell and having their first child. Yet the mood on this career-defining Number One country hit – which chronicled a man's wanderlust and apparently traced to a spat with Crowell (who produced the song!) – was an almost breezy reasonableness, as if the singer almost pitied the poor schnook. The melodic tick-tock was "Mellow Mafia" with a twangy moan, and Rosanne's tart aphorisms were some of the genre's most poetic. By Charles Aaron

65. Merle Haggard, ‘Okie from Muskogee’ (1969)

Not to be confused with Jimmy Patton's 1959 rockabilly track "Okie's in the Pokie," this megahit kicked Merle Haggard into the top tier of country performers. A Bakersfield-born son of Okie farmers, Haggard co-wrote this condemnation of pot smokers, sandal-wearers and draft-card burners on his tour bus with Strangers drummer Roy Edward Burris. Both parody ("pitching woo"? "Manly footwear"?) and counter-counterculture anthem – Hag once said its 24 lines contain "about 18 different messages" – "Okie" remains an undeniable a manifesto of ethnic pride.Haggard followed his relatively mellow Los Angeles studio original with a more truculent live version, then doubled down in January of the following year with his borderline-jingoist "The Fightin' Side of Me." Yet as he told a journalist decades later, "I didn't intend for 'Okie' to be taken as strongly from my lips as it was." By Richard Gehr

64. Patsy Cline, ‘I Fall to Pieces’ (1961)

Recorded as a single in 1961 and included on Patsy Cline Showcase that same year, this track has became a country ballad standard – but it almost wasn't. Producer Owen Bradley initially envisioned the track recorded by baritone Roy Drusky. According to Ellis Nassour's biography Honky Tonk Angel: The Intimate Story of Patsy Cline, Cline was standing in the hallway when she overheard Drusky turn it down because it wasn't manly enough. It ended up being his loss: Bradley agreed to let Cline take it over and she allegedly sang it so tenderly during sessions that it caused every man in the studio to cry. It became one of the first of several pop/country crossovers for Cline and charted for over six months. By Cady Drell

63. George Jones, ‘The Race Is On’ (1964)

A Top Five country hit in 1965, George Jones knew the ironic, upbeat number would be a hit the minute he heard it: "'The Race Is On' was pitched to me," he later told Billboard, "and I only heard the first verse, [sings] 'I feel tears welling up cold and deep inside like my heart's sprung a big leak,' and I said, 'I'll take it.'" Eight years later, the song took on new meaning when it became the first to be broadcast by New York's WHN, the crossover-friendly radio station that would set audience records and define the sound of pop country in the late-Seventies. By Linda Ryan

62. Emmett Miller, ‘Lovesick Blues’ (1928)

Obviously, the blackface aspect of Emmett Miller's act will forever shadow his legacy, but covers by everyone from Little Richard to Etta James to Ryan Adams to LeAnn Rimes are keeping "Lovesick" alive. Hank Williams didn’t learn everything he knew from Miller, but the sweet-singing 1920s minstrel performer did play a significant role inspiring country music's founding father. A couple decades before "Lovesick Blues" became Williams' first number one hit in 1949, Miller and his melancholy yodel were in love with a beautiful gal too. Miller’s version comes with a spoken intro in which he explains that he’s got "every known indication of being in that condition" before dappling the show tune, from the 1922 Tin Pan Alley musical Oh, Ernest, with some octave vaulting. For another take on Miller, hear David Lee Roth covering "Big Bad Bill (Is Sweet William Now)" on Van Halen’s Diver Down. By Reed Fischer

61. Ray Price, ‘Crazy Arms’ (1956)

After periods emulating both smooth Eddy Arnold and honky-tonkin' Hank Williams (whose Drifting Cowboys band he led after Hank's death), Ray Price (a.k.a. "the Cherokee Cowboy") returned to his Texas roots with this 1956 megahit that spent 20 weeks at the top of Billboard's country chart. Co-writer Ralph Mooney penned the tune after his wife left him due to his drinking, and its lyrics suggest deep emotional delirium and paranoia. The music, however, reflected Price's new shuffle style, with single-string fiddle, pedal steel guitar, and doubled acoustic and electric basses. Six months after Price's release, Jerry Lee Lewis's first Sun Records side was a more blatantly delirious rock cover that turned many heads. By Richard Gehr

60. Tennessee Ernie Ford, ‘Sixteen Tons’ (1955)

With its theatrical vocal, finger-snapping rhythm and a haunting clarinet hook seemingly borrowed from a Brecht/Weill musical, Tennessee Ernie Ford's excoriation of the evils of debt bondage was an unlikely country-pop smash. Although folksinger George Davis claimed to have written an original "Nine-to-Ten Tons" in the Thirties, Merle Travis countered that he wrote the more productive "Sixteen Tons" about his father's life in the coalmines of Muhlenberg County, Kentucky. The opening lines, meanwhile, came from a letter Travis's soldier brother wrote during World War II, and the Sisyphean refrain – "I owe my soul to the company store" – from his father's experience being paid in store tokens rather than cash. A blend of machismo and melancholy, "Sixteen Tons" has been covered by Elvis Presley, the Weavers, Stevie Wonder, Tom Morello and countless others. By Richard Gehr

59. Marty Robbins, ‘El Paso’ (1959)

Arizona native Marty Robbins' unusually long (4 minutes, 40 seconds) story-song is a barreling Greek tragedy adapted from the Mexican waltz-time ranchera country style. In what might be country's most cinematic hit, a narrator enamored of "wicked" Feleena shoots down a "dashing and daring" young cowboy who's hitting on her. Past tense becomes present as the narrator returns to El Paso, is shot himself by a vengeful posse and dies in Feleena's arms. Grady Martin's nylon-stringed guitar provides eloquent, flamenco-influenced instrumental commentary. A longtime staple of the Grateful Dead's cover repertoire, "El Paso" caught another cultural wave decades later when Feleena was transformed into "Felina," the anagrammatically allusive title of Breaking Bad's 2013 finale. By Richard Gehr

58. Jeannie C. Riley, ‘Harper Valley P.T.A.’ (1968)

"That song was my novel," songwriter Tom T. Hall once said of the epic "Harper Valley P.T.A." In this sassy 1968 takedown of small-town hypocrisy, a mini-skirted widow "socks it to" the titular busybodies – in its way, it was as innocence-ending as Bobbie Gentry's "Ode to Billie Joe" the previous year. Indeed, when singer Margie Singleton asked Hall to write her a similar song, the aspiring novelist took note of the Harpeth Valley Elementary School in Bellevue, Tennessee and found artistic inspiration in Sinclair Lewis's religion-mocking novel Elmer Gantry. Jeannie C. Riley's recording, however, made her the first woman to top both Billboard's Hot 100 and country-singles charts. Barbara Eden starred in both the 1978 comedy based on the song and in a 1981-82 TV show spun off the flick. By Richard Gehr

57. Eric Church, ‘Springsteen’ (2011)

It's not really about Bruce Springsteen, first of all. Though stadium-filling bad boy Eric Church's iPhone-lighter-app-waving triumph details "a love affair that takes place in an amphitheater between two people," the Boss was not the performer in question. Church politely but firmly declines to reveal the actual inspiration, which means the best country song of the 2010s thus far might have more accurately been titled "Nugent" or "Anka" or "Fogelberg." Cowritten by Church with Jeff Hyde and Ryan Tyndell, it's a dreamy, nostalgic weeper (tough as our man talks, he's a softie at heart) and drove 2011's Chief to dizzying heights. It even earned Church a handwritten thank-you note from Springsteen himself – scrawled on the back of a Fenway Park set list. By Rob Harvilla

56. Carrie Underwood, ‘Before He Cheats’ (2006)

This crossover smash emerged from circumstances as prefabricated as country music gets – written and produced by men whose credits include Lady Antebellum and Rascal Flatts, sung by an American Idol winner and sporting a literal-interpretation video. And yet the popcraft of "Before He Cheats," as rendered by Carrie Underwood in the key of frosty rage, is nearly perfect. Even a certified alt-country critical darling like Canadian singer-songwriter Kathleen Edwards is not immune to its seductive charms. "The rhythm of it, the metric of the lyrics, the chord changes, the play on words and unconventional patterns, the way she says 'Shania karaoke' – it's genius," Edwards said in 2009. "Fuck, I wish I'd written that!" By David Menconi

55. The Flatlanders, ‘Dallas’ (1990)

Perpetually unsung, the Flatlanders were a Lubbock trio who sounded like – well, there was Jimmie Dale Gilmore's flat, twangy voice; the warble of a singing saw; the lyrics that made sutras of psychedelic complexity sound like they were something Grandma crocheted into a throw pillow. Small-town, but more importantly, sensitive enough to address even the most routine insults of life in the 20th century, the big city didn't repulse them, but it did give them the willies. And yet in song, they are somehow always the eye of a storm: unchanging, know-nothing, happy to breathe deeply and just watch the show unfold. Would you be surprised to learn that they sank like a stone? By Mike Powell

54. Brad Paisley, ‘Alcohol’ (2005)

He rarely touches the stuff himself, but Brad Paisley's way with a booze anthem is unparalleled, and such range, too: "Whiskey Lullaby," a grim, suicide-haunted duet he cut with Alison Krauss in 2004, is basically Leaving Las Vegas in miniature, whereas this bawdy, self-penned waltz unleashed just a year later comes on like Animal House. A boastful first-person rundown of hooch's seductive powers – "I can make anybody pretty," it begins – that claims credit for everyone from Hemingway to the thoroughly soused best man at your wedding. It's a longtime live-show staple that inspires superfans to bring their own lampshades (seriously). "The song somehow seems to make the entire audience feel something in common," Paisley has marveled. "We're all out there together. We've all done it. We're all one big collective idiot. And there's nothing better than feeling that way." By Rob Harvilla

53. Charley Pride, ‘Kiss an Angel Good Mornin” (1971)

Charley Pride's 1971 recording of Ben Peters' "Kiss an Angel Good Mornin'" remains the definitive version of this a slightly naughty love song attempted by Conway Twitty, George Jones and Alan Jackson. The piano-driven arrangement here is classic early-Seventies countrypolitan, propelling the singer's only crossover Top 40 pop hit. Pride's métier has always been an easygoing effortlessness, which perfectly suits this ode to the pleasures and virtues of "Drunk in Love"-style domesticity. By David Menconi

52. Flatt and Scruggs, ‘Foggy Mountain Breakdown’ (1949)

If sparks flying off metal could sound sophisticated, they'd sound like Earl Scruggs' three-finger, five-string, five-alarm-fire banjo picking on this instrumental classic, which enshrined the banjo as a lead instrument in bluegrass. A stoic virtuoso from the western North Carolina boonies, Scruggs peppered the air with rippling eighth-note ragtime rolls on "Foggy Mountain Breakdown" (a song derived from an earlier track, "Bluegrass Breakdown," that he wrote for Bill Monroe), trading solo breaks with fiddler Benny Sims. Despite its innovative panache, the song only hit the country (and pop) charts after appearing as accompaniment to the car-chase scenes in Arthur Penn's scintillating, taboo-flaunting 1967 film Bonnie and Clyde. By Charles Aaron